Behind the Music

As the sun sets over Gloria Estefan's $35 million Star Island estate in Florida's Biscayne Bay, a boat built like the cartoon image of a pirate's vessel sails past her backyard and lets loose a cannonade of flashes from the camera-toting tourists on board. "Everyone wave to the pirate ship!" Estefan, 46, says to her staffers and two kids. Then, turning to her son, she asks, "Remember how you used to greet them?"

Nayib, 23, does recall his boyhood greeting—and the ensuing punishment: "I had to write, like, 3,000 times, 'I will not moon the tour boats.'"

"I made him do it maybe 1,000 times," counters Gloria. "I didn't want people to think it was me! He had to take it like a big boy."

These days Mama's goateed, 5'11" boy is entertaining the crowds in a less cheeky way: deejaying at Miami Beach nightclubs while trying to launch a directing career. His new film, Famous, created at Gloria's request as a free DVD accompaniment to her 24th CD, Unwrapped, "is not a love letter to my mom," says Nayib, who went on tour with his parents at 5 and performed with them at the Olympics at age 15. But it is "a thank-you to my parents for all the good times we've had."

Made for just $60,000 and shot over a nine-month period in 2002 and 2003, the documentary weaves scenes of him with his parents and sister Emily, 8, with concert excerpts and backstage vignettes. "He used home movies, me in a men's bikini, fat, skinny, asleep—my reputation is ruined!" dad Emilio, 50, jokes. The film owes many of its lighter moments to the youthful antics of Nayib (whose name means "the good one" in Arabic) himself: In one scene he wins an award at school but walks down the stairs backward after receiving it. In another his mom is yelling at him while he pours water on a new bedroom set. Until she saw the film, Estefan reflects, "I didn't realize how much I said, 'Nayib!'"

It wasn't until he turned 17 that Nayib, who'd been thrown out of private school in 10th grade for crank-calling a classmate's parent and wound up graduating from South Miami Senior High School, was diagnosed with attention deficit disorder. But after six months on medication, he quit. "I didn't like it," he says. "I chose to stay a little bit distracted and use my eccentricity for writing scripts and deejaying."

A movie buff since childhood, he enrolled in the Los Angeles Film School. After graduating in 2001, he spent a year in London and was an A&R talent scout for Sony. Missing the Florida sunshine, he returned home in 2002 to a South Beach apartment and went to work on Famous. Aside from deejaying and writing a horror-film script, tentatively called Tapeworm, Nayib, who's currently unattached, "is pretty hermetically sealed," says Gloria, who adds that she's only met two of his past girlfriends.

Mom's life, on the other hand, is now an open book, thanks to her son. "There's so many other things to be said, but I didn't have time for all the clips," says Nayib. Like what? "She fell off the stage once. She's lucky I didn't include that one."